O-Cresol → Ethyl (4-mercapto-2-methylphenoxy)acetate

HRID 1014070

반응식

HRID 1014070 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([S:13]CC2SC(C3C=CC(C(F)(F)F)=CC=3)=NC=2C)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11].[C:31]1(C)C(O)=CC=C[CH:32]=1.S(Cl)(Cl)(=O)=O.[Sn]>>[SH:13][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH2:31][CH3:32])=[O:11])=[C:2]([CH3:1])[CH:3]=1

참가 물질

5

반응물 4

HCID 335O-CresolHCID 24648Sulfuryl chlorideHCID 5352426Tin atomHCID 9803963GW 5015162회

생성물 1

HCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetate

실험 절차

As an alternative synthesis method of GW501516, it is disclosed, as illustrated in the following scheme (2), that the compound (13) of GW501516 can be prepared by introducing ethyl acetate group to o-cresol (14), reacting the resulted compound (15) with sulfonyl chloride, reducing the resulted compound (16) with tin (Sn) under acidic condition to form ethyl (4-mercapto-2-methyl phenoxy)acetate (17), reacting it with 5-chloromethyl-4-methyl-2-(4-trifluoromethyl phenyl)thiazole (11) together with an excessive cesium carbonate to obtain the ethyl ester intermediate (18) of GW501516, and deprotecting the ester group of the intermediate compound with 1N lithium hydroxide.

후처리

  1. customcan be prepared

출처 및 근거

ORD 기록
ord-3293be9e9c0b4cc88b6f07357881eafa
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07982050B2

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